Acetonitrile → 3-(5-Fluoro-2-pyridyl)-5-(3-(1-benzyl-1,2,5,6-tetrahydropyridin-3-yl)-5-fluorophenyl)-1,2,4-oxadiazole

HRID 2216872ノート

反応式

HRID 2216872 の反応式
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]=[C:11]([C:13]3[CH:18]=[C:17]([C:19]4[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=4)[CH:16]=[C:15]([F:25])[CH:14]=3)[O:10][N:9]=2)=[N:6][CH:7]=1.C(#N)C.[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]=[C:11]([C:13]3[CH:14]=[C:15]([F:25])[CH:16]=[C:17]([C:19]4[CH2:20][N:21]([CH2:29][C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[CH2:22][CH2:23][CH:24]=4)[CH:18]=3)[O:10][N:9]=2)=[N:6][CH:7]=1

参加物

6

反応物 4

HCID 6342AcetonitrileHCID 7498Benzyl BromideHCID 4311764Sodium borohydrideHCID 101318283-(5-Fluoro-2-pyridyl)-5-(3-fluoro-5-(3-pyridyl)phenyl)-1,2,4-oxadiazole

生成物 1

HCID 101135083-(5-Fluoro-2-pyridyl)-5-(3-(1-benzyl-1,2,5,6-tetrahydropyridin-3-yl)-5-fluorophenyl)-1,2,4-oxadiazole収率 8%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

In a screw cap vial equipped with stir bar added 3-(5-Fluoro-2-pyridyl)-5-(3-fluoro-5-(3-pyridyl)phenyl)-1,2,4-oxadiazole (100 mg, 0.30 mmol), acetonitrile (2 ml) and benzyl bromide (0.05 ml, 0.39 mmol). Stirred the resulting mixture at 90° C. for 4 h. Cooled the mixture to room temperature, concentrated in-vacuo and triturated the residue with 30% ethyl acetate in hexanes to isolate the quarternary salt. The isolated solid was dissolved in methanol (2 ml) and treated with sodium borohydride (22.6 mg, 0.60 mmol) at 0° C. The bright yellow reaction mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated in-vacuo and the residue was dissolved in dichloromethane (20 ml). The organic phase was sequentially washed with water (20 ml) and brine (20 ml), dried (sodium sulfate), filtered and concentrated in-vacuo. The crude residue was purified on silica gel using 30% ethyl acetate in hexanes to isolate the title compound (10.1 mg, 8%) as yellow oil. 1H-NMR (CDCl3), δ (ppm): 8.69 (d, 1H), 8.26 (dd, 1H), 8.02 (s, 1H), 7.80 (dd, 1H), 7.60 (dt, 1H), 7.32 (m, 6H), 6.34 (m, 1H), 3.73 (s, 2H), 3.40 (bs, 2H), 2.63 (t, 2H), 2.39 (m, 2H).

後処理

  1. customIn a screw cap vial
  2. customequipped
  3. stirringStirred the resulting mixture at 90° C. for 4 h
  4. concentrationconcentrated in-vacuo
  5. customtriturated the residue with 30% ethyl acetate in hexanes
  6. customto isolate the quarternary salt
  7. stirringThe bright yellow reaction mixture was stirred at room temperature for 2 h
  8. concentrationThe reaction mixture was concentrated in-vacuo
  9. dissolutionthe residue was dissolved in dichloromethane (20 ml)
  10. washThe organic phase was sequentially washed with water (20 ml) and brine (20 ml)
  11. dry with materialdried (sodium sulfate)
  12. filtrationfiltered
  13. concentrationconcentrated in-vacuo
  14. customThe crude residue was purified on silica gel using 30% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-1ad16702f26b4023b1217c61945332b2
出典データセット
uspto-grants-2006_09
特許番号
US07112595B2

反応ノート

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